Routes to highly substituted thiophenol derivatives

Gary Nicholson; Jon D. Silversides; Stephen J. Archibald

doi:10.1016/j.tetlet.2006.07.039

Routes to highly substituted thiophenol derivatives

Gary Nicholson, Jon D. Silversides, Stephen J. Archibald^*

^*Corresponding author for this work

Imaging Chemistry & Biology

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Syntheses of highly substituted thiophenol derivatives that incorporate steric bulk into the ligand framework via ortho and para tert-butyl substituents are reported. S-Benzyl and trityl protection were investigated and the effects of substituents on the Newman-Kwart rearrangement of the thiocarbamate discussed. Single crystal X-ray structures are reported for three compounds and demonstrate the role of hydrogen bonding in stabilising the thiophenol to oxidation.

Original language	English
Pages (from-to)	6541-6544
Number of pages	4
Journal	TETRAHEDRON LETTERS
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.039
Publication status	Published - 11 Sept 2006

Keywords

Protecting group
Radical
Thiophenol

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10.1016/j.tetlet.2006.07.039

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AU - Nicholson, Gary

AU - Silversides, Jon D.

AU - Archibald, Stephen J.

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N2 - Syntheses of highly substituted thiophenol derivatives that incorporate steric bulk into the ligand framework via ortho and para tert-butyl substituents are reported. S-Benzyl and trityl protection were investigated and the effects of substituents on the Newman-Kwart rearrangement of the thiocarbamate discussed. Single crystal X-ray structures are reported for three compounds and demonstrate the role of hydrogen bonding in stabilising the thiophenol to oxidation.

AB - Syntheses of highly substituted thiophenol derivatives that incorporate steric bulk into the ligand framework via ortho and para tert-butyl substituents are reported. S-Benzyl and trityl protection were investigated and the effects of substituents on the Newman-Kwart rearrangement of the thiocarbamate discussed. Single crystal X-ray structures are reported for three compounds and demonstrate the role of hydrogen bonding in stabilising the thiophenol to oxidation.

KW - Protecting group

KW - Radical

KW - Thiophenol

UR - http://www.scopus.com/inward/record.url?scp=33746834489&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.07.039

DO - 10.1016/j.tetlet.2006.07.039

M3 - Article

AN - SCOPUS:33746834489

SN - 0040-4039

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SP - 6541

EP - 6544

JO - TETRAHEDRON LETTERS

JF - TETRAHEDRON LETTERS

IS - 37

ER -

Routes to highly substituted thiophenol derivatives

Abstract

Keywords

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